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39 Evergreen Ave, Key Haven
$5,400,000
8 Beds ⋅ 10 Baths ⋅ 616954 MLS
Tucked within an exclusive Key Haven cul-de-sac, Casa di Sempre is a European-inspired waterfront estate offering more than 260 linear feet of water frontage across two sides of the property, including 200 feet of concrete dockage for boating enthusiasts. Resting on over 15,000 square feet of land, this residence showcases superior craftsmanship and thoughtful design throughout more than 6,500 square feet of refined living space. The main residence features five bedrooms and four-and-a-half baths, while a three-bedroom, three-bath guest villa provides privacy and comfort for visitors. Constructed of 11-inch insulated concrete forms with poured concrete floors and stairs, the home provides extraordinary strength, safety, and sound insulation. Impact glass windows and doors are complemented by hidden European-style roll-down shutters, ensuring both security and elegance. Inside, an open gourmet kitchen, formal dining room, study, and three fireplaces create a warm yet sophisticated ambiance. Eight-foot mahogany interior doors and windows elevate each space with timeless craftsmanship. Outdoors, the estate is a true entertainer's haven, highlighted by a 65-foot heated glass-mosaic pool with a 21-foot infinity edge, three cascading waterfalls, and an island with a six-seat swim-up bar leading to a custom cabana. A private 400-square-foot gym and 3,800-square-foot garage complete the amenities, along with a generator and fire suppression system for added peace of mind. A rare combination of elegance, engineering, and waterfront grandeur, Casa di Sempre represents one of the most remarkable estates in the Lower Florida Keys—crafted for those who value strength, sophistication, and sanctuary by the sea.

39 Evergreen Ave, Key Haven

33 Cypress Ave, Key Haven
$3,250,000
4 Beds ⋅ 5 Baths ⋅ 615813 MLS
Enjoy sweeping water views from this exceptional Key Haven home overlooking Cypress Lake. With 4 spacious bedrooms and 4.5 baths, the residence blends comfort and luxury in every detail. Built in 2007 with superior materials and craftsmanship, highlights include a standing seam copper roof, Saturnia stone, and hickory wood floors throughout. From the grand foyer, water views unfold throughout the home. A graceful staircase leads to a second living area and three ensuite bedrooms, each with private balconies. The primary suite can be found on either level, offering flexibility in layout. The kitchen features custom cabinetry, granite counters, stainless steel appliances, wine cooler, icemaker, and both a breakfast room and formal dining area. Relax by the heated pool and covered patio or take in the waterfront from nearly every room. Additional features include tall coffered ceilings, impact-resistant windows, a protected seawall, and strong curb appeal. Designed with care and built to last, this is one of Key Haven's finest offerings & almost feels like open water living.

33 Cypress Ave, Key Haven

13 Arbutus Dr, Key Haven
$2,150,000
4 Beds ⋅ 3 Baths ⋅ 616022 MLS
Welcome to 13 Arbutus Drive, an exceptional waterfront residence located in the coveted Key Haven community—just minutes from vibrant Key West, yet worlds away in peace and privacy. This beautifully maintained home offers the ideal blend of indoor-outdoor living with expansive canal views, deepwater boating access, and luxury finishes throughout, with all impact windows and doors. Bathed in coastal chic design this property offers four (4) bedrooms and three (3) bathrooms, including a primary suite with water views, a walk-in closet, and a spa-like bath. Step inside to discover an open-concept living space bathed in natural light, with a seamless flow between the living, dining, and kitchen areas—perfect for entertaining. The updated chef's kitchen features a stainless steel gas range, custom cabinetry, and large island. Oversized sliding glass doors open to a covered patio with additional dining area, and private pool with waterfall, creating your own tropical oasis. Outside, enjoy 60 feet of concrete seawall with boat lift (6K)—ready for your boat and immediate access to the open water. The lushly landscaped lot includes low-maintenance turf, landscape lighting, off street parking, and ample storage. There is also the must have outdoor shower for that after boating day rinse off. Live the dream and schedule your private tour today!

13 Arbutus Dr, Key Haven

1 Bougainvillea Ave, Key Haven
$2,100,000
5 Beds ⋅ 3 Baths ⋅ 620153 MLS
Welcome to luxury waterfront living in sought-after Key Haven. Completely reimagined by Affiliated Builders, this stunning residence offers the perfect blend of sophisticated design, modern functionality, and island lifestyle. This home has been thoughtfully renovated with gorgeous designer finishes and meticulous attention to detail, creating a truly turnkey coastal retreat. The spacious floor plan features 2086 sq foot, 4 bedrooms plus a flexible office/living space that can easily serve as a 5th bedroom, along with a dedicated laundry room, mudroom, and 1-car garage. At the heart of the home is a spectacular gourmet kitchen and dining complete with premium Bosch & Bertazzoni appliances, quartz countertops, and custom cabinetry designed for both everyday living and entertaining. Custom built-in closets throughout the home add both style and functionality. Step outside to your private waterfront oasis featuring a heated and chilled custom saltwater pool surrounded by elegant limestone decking, creating the ultimate setting for relaxing or entertaining year-round. Boaters will appreciate the 10,000-pound boat lift accommodating up to a 25-foot boat, offering quick access to the beautiful waters of the Florida Keys. Additional upgrades include a whole-house Generac generator, irrigation system, and countless high-end improvements throughout. Furniture is negotiable, making this exceptional Key Haven property ready to enjoy immediately.

1 Bougainvillea Ave, Key Haven

52 Key Haven, Key Haven
$2,055,000
4 Beds ⋅ 4 Baths ⋅ 620883 MLS
Getting out on the water is simple from this beautifully remodeled 4-bedroom, 4-bath home, and coming home feels just as inviting. Set along a wide canal, the property offers quick access to open water with no fixed bridges. A private pool and inviting indoor-outdoor living spaces make being at home just as enjoyable as a day on the water. Inside, the open layout feels bright, spacious, and thoughtfully designed, with impact-rated windows and doors throughout. The kitchen is finished with KraftMaid cabinetry, quartz countertops, and stainless steel appliances, creating a clean space that connects naturally with the main living area. Impact-rated folding sliders open fully to a 450 sq. ft. covered lanai, making the home ideal for entertaining or unwinding. The spacious primary suite includes a walk-in closet and an updated bathroom with a rainfall shower head. One of the guest bedrooms also features a walk-in closet, adding valuable storage and comfort. Porcelain tile flooring runs throughout the main home, while arched architectural details inside and out give the property a distinctive sense of character. The outdoor area offers the kind of setting that makes it easy to lose track of time, with 1.25' Shellstone pavers, covered patio space, privacy fencing, and a full bathroom conveniently located off the pool deck. Along the canal, the concrete seawall offers excellent dockage and room for a future boat lift. Additional features include two-zone air conditioning, two on-demand water heaters, brand new PVC plumbing throughout, upgraded electrical, a detached poolside cabana with electricity. Located in Key Haven, just minutes from Key West, this home brings together privacy, thoughtful updates, excellent boating access, and the easy indoor-outdoor lifestyle that makes the Florida Keys so special.

52 Key Haven, Key Haven

19 Azalea Dr, Key Haven
$1,800,000
3 Beds ⋅ 2 Baths ⋅ 617801 MLS
Stunning, canal-front Key Haven home, with one turn to open water, offering quick access to both Gulf and Atlantic. Key Haven is a boater's paradise and is just a few miles to the action of downtown Key West. 60 feet of water frontage, concrete seawall, 10k boat lift, davits and swim ladder are all ready for you to enjoy island living and our beautiful surrounding waters. This canal is deep and wide, with visibility to the bottom and fish GALORE! Enjoy the ease and flow of living in a ground level waterfront home along with the security of a significantly elevated lot that rises high above street level. This home has it all: concrete in structure, just shy of 2000 sf, three bedrooms and two full baths. Enormous open kitchen, dining and two living areas blend seamlessly and look out on to the sparkling, wide canal and covered patio. Renovated kitchen with stainless steel appliances, double oven and an 8 burner Viking gas stove. The entire house has newer porcelain tile floors throughout and freshly painted rooms. Connected to the home is a rare, coveted 420 sf garage for your vehicles, workshop, storage and laundry. There is also considerable storage above the garage accessible by two pull-down ladders. The rear of the property is a dream, allowing for multiple outside living areas. The expansive tiled patio is great for entertaining and easy to maintain. The patio roof runs the entire width of the home, allowing for both shaded and sunny areas to enjoy. The outdoor, concrete bar with sink, refrigerator, grill and tv is perfect for entertaining and relaxing. 19 Azalea sits four houses back from the main canal into the Gulf, also four houses from the end of the street. This is a dead-end road with no pass through traffic. Key Haven is known for its sense of community, peaceful vibe, and stellar boating. Here you can enjoy quiet night walks under the stars, caring neighbors, soothing ocean breezes and crystal clear Keys waters right from own back yard.

19 Azalea Dr, Key Haven

30 Key Haven, Key Haven
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 617149 MLS
Discover the perfect blend of modern luxury and coastal living in this completely renovated 2,715 sq. ft. concrete home set on a 75-foot-wide canal. Every detail has been thoughtfully designed to deliver style, comfort, and peace of mind—with impact-rated windows and doors, a metal roof, and low insurance costs. New electrical wiring and panel, plumbing, HVAC, and more with HOME WARRANTY. This 3-bedroom, 3-bath residence offers all ensuite bedrooms, each with a touch of elegance and privacy. The open-concept kitchen features custom cabinetry with matching appliance fronts, waterfall-edge luxury quartz countertops, a custom range hood, and a pot filler. A coffee bar and dual-climate wine fridge make entertaining effortless, while the spacious laundry room adds functionality and storage. The luxurious primary suite includes sliding doors leading to a private covered terrace—your personal retreat overlooking the canal. Bathrooms feature designer finishes with spa-like appeal, combining sophistication and relaxation. Boating enthusiasts will love the wide, deep canal with room to dock and quick access to open water. 60 ft concrete seawall is permitted and ready for new owner to call their own. There's ample space for a pool and plenty of parking for guests, trailers, or toys. Located in one of the most desirable family-friendly neighborhoods, this home offers the lowest price per square foot in its class—an unbeatable opportunity for luxury living in the Keys.

30 Key Haven, Key Haven

16 Bamboo, Key Haven
$1,475,000
3 Beds ⋅ 2 Baths ⋅ 619146 MLS
Pristine canal front living on KEY HAVEN with a 55 foot concrete seawall on spectacular Bamboo Terrace. WATERFRONT. TURN-KEY and BEAUTIFUL. This ''needs nothing'', fully furnished home sits tucked away on a dead-end cul-de-sac. Tropical oasis with no cut through traffic on an over 6000 sf lot. TWO BOAT LIFTS. Custom, brick-paved front and back yard, river rock and beautiful palms create a serene oasis along with the joy and ease of low-maintenance landscaping. Off-street, covered parking, trailer storage, fully fenced yard with sliding driveway gate. Air conditioned work shop/ laundry room and storage galore. Meticulous interior with newer, gorgeous furnishings. Custom kitchen with solid cherry wood cabinetry, stainless steel appliances and quartz counters. Large dining room and HUGE living room - all open. Spacious primary en-suite with walk-in closet and two generous guest rooms, both with double closets and a shared full bath. All closets are cedar lined. Updated bathrooms, fresh paint throughout home, ceiling fans, and custom plantation shutters line the inside of all windows and sliders. New AC system in 2021, metal roof was replaced in 2013 and all windows and doors have hurricane rated panels for storm protection. Sunsets are lovely and peaceful from your backyard. The water and lush vegetation sparkle with hues of gold and pastel. Covered patio off the primary suite, cheekie hut with grill, multiple areas outside to lounge, sunbathe and dine. SIde yard with low maintenance turf, great for pets. Paddle boards and kayaks convey with the sale, along with 4 e-bikes!! Quick zip to deep, open water from your seawall (see map in photos). Excellent opportunity to enter into the exclusive Key Haven market. Deep water boating from your backyard and only minutes to shopping and the world-renowned activities and vibrance of downtown Key West.

16 Bamboo, Key Haven

3 Birchwood Dr, Key Haven
$907,500
3 Beds ⋅ 1 Baths ⋅ 618249 MLS
Tucked away on a quiet street, 3 Birchwood Drive represents a rare chance to own in one of the most sought after neighborhoods near Key West, at a price point rarely seen. This 3 bedroom, single level home has been lovingly cared for and thoughtfully improved over the years. The kitchen was remodeled in 2019 and serves as the heart of the home, complete with a high end Bosch appliance package including an induction range that makes everyday cooking feel effortless. Porcelain tile floors flow throughout, creating a clean, cohesive feel, while updated interior doors and fresh paint inside and out add to the move in ready appeal. The screened in rear porch becomes an extension of the living space, perfect for morning coffee, evening breezes, or quiet downtime. Outside, the fully fenced yard with added landscaping provides privacy and room to enjoy island living without excess maintenance. This is one of the least expensive homes in Key Haven. Opportunities like this do not come along often, and when they do, they move quickly.

3 Birchwood Dr, Key Haven

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